No matter how well you know Chicago, you most likely don’t know about these hidden secrets. Dig in.

1. There’s an alleyway paved entirely with wooden blocks between the State Parkway and Astor Street, behind the Archbishop’s residence. It’s a relic of when the city made sidewalks out of the material in 1850’s and led to the streets literally burning in the Great Chicago Fire.

Screen Shot 2016-08-29 at 1.56.15 PMArc Chicago

2. The City of Chicago gives out actual awards to people who shovel their sidewalks the best in the snowy months. They’re called “Winter Wonders,” and are signed by the Mayor’s Pedestrian Advisory Council.

5422942263_77bd539411_ovxla via Flickr

3. Grab your binoculars—there’s a historic shipwreck in the waters of Lake Michigan that is visible from the coast, off 49th Street Beach.

8755621230_af522f876d_oJosh Mogerman via Flickr

4. There is an adorable kissing rock devoted to the site where President and Michelle Obama had their first date at 53rd and South Dorchester, which used to be a Baskin Robbins.

Screen Shot 2016-08-29 at 2.07.02 PMdavidestekarn via Instagram

5. You can get some of the best pastries in the city out of a window down an alleyway in Lincoln Park. Just head west down Armitage from Halsted and follow the baking aromas to the right.

Screen Shot 2016-08-29 at 2.10.43 PMfef_may via Instagram

6. There is an abandoned street that runs under some of the best-known buildings in River North—Carroll Avenue. Formerly the entrance to the Kenzie Bridge, one of the most-trafficked freight lines of the 20th century, the path is now only haphazardly reached on foot.

7354946088_4bb322175a_k (1)Jeysin Trevino via Flickr

7. Due to a train accident that killed a ton of circus performers in 1918, there are several gravestones of clowns like “Baldy” and “Smiley” and even elephants in Woodlawn Cemetery.

6295718090_0b2ab636b0_bColleen MacMahon via Flickr

8. There is a sculpture dedicated to dog poop called “Shit Fountain” at 1001 North Wolcott Avenue. Since it sits on private property, the city has left it alone.

6237143509_49affbb06c_bJake Trussell via Flickr

9. When winter sucks, there’s a path called the Pedway under the Loop that will let you avoid going aboveground. It’s currently larger than 40 city blocks and growing larger all the time. (It’s such a mystery that even Tribune reporters get tripped up by it.)

16258585239_28491faf00_hJohn Greenfield via Flickr

 [Featured Image: Roman Boed via Flickr]


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